CN101182302B - Method for preparing compositions containing zeaxanthin - Google Patents
Method for preparing compositions containing zeaxanthin Download PDFInfo
- Publication number
- CN101182302B CN101182302B CN2007101589121A CN200710158912A CN101182302B CN 101182302 B CN101182302 B CN 101182302B CN 2007101589121 A CN2007101589121 A CN 2007101589121A CN 200710158912 A CN200710158912 A CN 200710158912A CN 101182302 B CN101182302 B CN 101182302B
- Authority
- CN
- China
- Prior art keywords
- zeaxanthin
- solvent
- preparation
- sodium
- xenthophylls
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 title claims abstract description 81
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 title claims abstract description 79
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 title claims abstract description 79
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 title claims abstract description 79
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 title claims abstract description 79
- 235000010930 zeaxanthin Nutrition 0.000 title claims abstract description 79
- 239000001775 zeaxanthin Substances 0.000 title claims abstract description 79
- 229940043269 zeaxanthin Drugs 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 36
- 239000000203 mixture Substances 0.000 title claims description 46
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000019253 formic acid Nutrition 0.000 claims abstract description 11
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 7
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 6
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 239000012065 filter cake Substances 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 239000003963 antioxidant agent Substances 0.000 claims description 22
- 230000003078 antioxidant effect Effects 0.000 claims description 22
- 235000006708 antioxidants Nutrition 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000004250 tert-Butylhydroquinone Substances 0.000 claims description 13
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000012752 auxiliary agent Substances 0.000 claims description 12
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 10
- 238000001953 recrystallisation Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 238000004140 cleaning Methods 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- 229930003427 Vitamin E Natural products 0.000 claims description 5
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 5
- 235000019165 vitamin E Nutrition 0.000 claims description 5
- 239000011709 vitamin E Substances 0.000 claims description 5
- 229940046009 vitamin E Drugs 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000019154 vitamin C Nutrition 0.000 claims description 4
- 239000011718 vitamin C Substances 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
- 229930014626 natural product Natural products 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 2
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 2
- 229960005055 sodium ascorbate Drugs 0.000 claims description 2
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 238000005815 base catalysis Methods 0.000 abstract 2
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 32
- 238000010438 heat treatment Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 235000005881 Calendula officinalis Nutrition 0.000 description 17
- 241000736851 Tagetes Species 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- 239000000049 pigment Substances 0.000 description 12
- 239000003513 alkali Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000002798 spectrophotometry method Methods 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 235000012680 lutein Nutrition 0.000 description 2
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 description 2
- 239000001656 lutein Substances 0.000 description 2
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 description 2
- 229960005375 lutein Drugs 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- -1 fatty acid salt Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000009774 resonance method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- JKQXZKUSFCKOGQ-QAYBQHTQSA-N zeaxanthin Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-QAYBQHTQSA-N 0.000 description 1
- 150000003749 zeaxanthins Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a preparation method of a combination containing zeaxanthin. The method comprises the steps of the base catalysis isomerization reaction and is characterized in that catalyst used for the base catalysis isomerization reaction consists of alkaline catalyst and additive which is selected from formic acid, acetic acid, oxalic acid, propionic acid or sodium borohydride. The preparation method of the combination containing zeaxanthin of the present invention has short technical route, low production cost, high yield and the high purity of the product, does not produce toxic and harmful waste and is applicable to the industrialized production.
Description
Technical field
The present invention relates to the xenthophylls in the natural plant extracts and ester thereof are changed into the method for zeaxanthin, relate in particular to the method for utilizing the alkali isomerization reaction to produce zeaxanthin.
Background technology
Zeaxanthin (zeaxanthin, 3,3 '-dihydroxyl-β-Hu Luobusu) is the carotenoid that nature extensively exists.In recent years, the investigation of massive epidemiology and studies show that, zeaxanthin has special physiological properties at the generation and the aspects such as development, minimizing cardiovascular disease incidence rate, raise immunity and vision protection that reduce cancer.In addition, there are some researches show: take in a large number zeaxanthin can reduce cataractous probability.Also there are some researches show: trans zeaxanthin has higher stability than the cis zeaxanthin, and more effective coloring effect is arranged.
Narrated among the PCT patent disclosure WO96/02594 a kind of under controlled temperature and pressure condition in strong alkali solution xenthophylls be isomerizated into the method for zeaxanthin.Used alkali is alkali metal hydroxide, calcium hydroxide, yellow soda ash, ammonium hydroxide or organic bases, and thing is not ethamine, thanomin or morpholine.Water is as solvent.The yield of zeaxanthin can reach 24% in this way; But do not speak of isomerization reaction and produced how many degradation productions.Similarly, this yield also is unsuitable for industrial production.
Summary of the invention
The object of the present invention is to provide a kind of highly purified preparation of compositions method that contains zeaxanthin.
Goal of the invention of the present invention is achieved by the following technical solution:
The preparation of compositions method that contains zeaxanthin of the present invention comprises the step of alkali isomerization reaction, it is characterized in that catalyzer that described isomerization reaction is used is alkaline catalysts or the mixed catalyst be made up of alkaline catalysts and auxiliary agent, described auxiliary agent is selected from formic acid, acetate, oxalic acid, propionic acid or sodium borohydride.The use of auxiliary agent is the present inventor result serendipitous at work, experimental results show that, in above-mentioned reaction, make used additives help to improve zeaxanthin in the product: the ratio of xenthophylls, promptly increased the transformation efficiency of xenthophylls, improved the output of zeaxanthin.
The above-mentioned preparation of compositions method that contains zeaxanthin is included in the closed reactor, will through or be dissolved in organic solvent through pretreated natural product or the xenthophylls that contains xenthophylls, and add the alkaline catalysts of 2～20M and the auxiliary agent of raw materials quality 0.01～5%, under 90～130 ℃ of conditions of temperature, react 12～36h.
Auxiliary agent preferable formic acid or sodium borohydride in the above-mentioned preparation of compositions method that contains zeaxanthin.
Alkaline catalysts is the conventional catalyst of isomerization reaction in the above-mentioned preparation of compositions method that contains zeaxanthin, mostly be basic catalyst, preferred sodium hydroxide, calcium hydroxide, potassium hydroxide, sodium methylate, sodium ethylate, yellow soda ash, salt of wormwood, sodium bicarbonate, saleratus, potassium methylate or potassium ethylate among the present invention.Especially preferred sodium hydroxide or potassium hydroxide.
In the above-mentioned preparation of compositions method that contains zeaxanthin, the mixed solvent that two or more solvent is formed with arbitrary proportion in the preferred hexane of the employed solvent of isomerization reaction step, heptane, sherwood oil, methyl alcohol, ethanol, Virahol, propyl carbinol, benzene, toluene or the above-mentioned solvent.
Particularly, the preparation of compositions method that contains zeaxanthin of the present invention comprises the steps:
1. in reactor, add reaction raw materials, organic solvent, isomerization reaction alkaline catalysts and auxiliary agent, wherein, the consumption of organic solvent is 5～12 times of (volumes: quality) of reaction raw materials; Base catalyst concentration is 2～10M; Described auxiliary agent is formic acid or sodium borohydride, and its addition is 0.1～3% of a raw materials quality;
2. in the closed reactor, nitrogen replacement at pressure 0MPa～4MPa, reacts 12～36h under 90～130 ℃ of conditions of temperature;
3. behind the stopped reaction, be cooled to 40～80 ℃, filter;
4. the gained filter cake is washed 3～8 times with cleaning solvent, described cleaning solvent is selected from water, methyl alcohol, ethanol, Virahol, normal hexane, sherwood oil or acetone, and each time washing can be chosen different cleaning solvents;
5. washed after-filtration, added antioxidant, 30～80 ℃ of oven dry 2～24h.
According to the state of the art, isomerization reaction need be carried out under the anaerobic air tight condition, and the means that the present invention takes to vacuumize reach oxidation resistant purpose.
Under condition described in the invention, heating still can keep higher product yield more than 36 hours under 90～130 ℃ of temperature.Though mentioned temperature of reaction in other patent in 40～120 ℃ of scopes, heating does not also have patent to accomplish for a long time under comparatively high temps.
In the aforesaid method of the present invention, step purpose 4. is two kinds of catalyzer in the cleaning reaction, also has some other pigment and vegetable jelly, the fatty acid salt that reaction generates.Cleaning solvent preferably water, methyl alcohol, ethanol or sherwood oil.Especially particular methanol.
In the above-mentioned preparation of compositions method that contains zeaxanthin of the present invention, the antioxidant of step in 5. is selected from TBHQ, vitamin-E, vitamins C, sodium ascorbate, dimension C cetylate, BHT or above-mentioned two or more antioxidant mixes the mixture of forming with arbitrary proportion.
Promptly can obtain the product of zeaxanthin quality percentage composition 30～80% according to aforesaid method,, can behind washing step, make with extra care product in order further to obtain the higher product of target product content.The purified concrete grammar is a recrystallization, carries out recrystallization after the employing extraction solvent extracts fully; Wherein, extraction solvent is selected from chloroform, tetrahydrofuran (THF), ethyl acetate, acetone or methylene dichloride; Recrystallization solvent is selected from chloroform, tetrahydrofuran (THF), ethyl acetate, acetone, methylene dichloride, or mixed solvent that mix to form with arbitrary proportion of two or more solvent wherein.Above-mentioned recrystallization temperature preferably is lower than 6 ℃.
The preparation method who has added above-mentioned recrystallizing and refining purification step can make the product of zeaxanthin percentage quality percentage composition 80～92%.
The preparation of compositions method processing technology routine flow process that contains zeaxanthin of the present invention is short, production cost is low, yield is high, product purity is high, and does not have the poisonous and harmful refuse and produce, and is fit to suitability for industrialized production.
Embodiment
If no special instructions, embodiments of the invention all adopt spectrophotometry in conjunction with the content of pigment content total in the efficient liquid phase chromatographic analysis product, zeaxanthin and calculating (zeaxanthin: ratio xenthophylls), and utilize the method for nucleus magnetic resonance to detect the steric configuration of product:
1. the mensuration of zeaxanthin (xenthophylls) total pigment
Present method adopts spectrophotometry under 450nm the total pigment of zeaxanthin (xenthophylls) to be measured:
(1) reagent and solution
Normal hexane: analytical pure;
Methyl alcohol: analytical pure;
Acetone: analytical pure, dry and do not contain ethanol, add zinc granule (10 order) distillation before using;
Lysate: normal hexane: acetone: methyl alcohol=80: 10: 10;
(2) instrument: spectrophotometer: 752 types
(3) determination step
Weighing m g (accurately to 0.0002g) zeaxanthin (xenthophylls) sample, dissolving and constant volume in v mL lysate.Dilute, extension rate is d again.Under 450nm, adopt its absorbance A of spectrophotometric determination.In order to guarantee higher accuracy, the volume of control solution makes A between 0.25 and 0.75.
(4) method of calculation
The total pigment X that zeaxanthin (xenthophylls) is represented with the quality percentage
l(%), be calculated as follows:
Wherein:
A is the absorbancy of sample under 450nm;
V is a sample initial dissolution volume, and unit is a milliliter (mL);
D is the diluted sample multiple;
M is the quality of sample, and unit is gram (g);
The 2348th, the optical density value of xenthophylls when measuring wavelength.
2. the measuring method formed of zeaxanthin pigment
Present method adopts high performance liquid chromatography that zeaxanthin pigment composition is separated and analyzes, calculate the content of zeaxanthin pigment, the absolute content=total pigment of zeaxanthin pigment * pigment percentage composition in conjunction with the above-mentioned total pigment content of measuring with spectrophotometric method.Specific analytical method is with reference to Application of HPLCcoupled with DAD, method in APCI-MS and NMR to the analysis of lutein and zeaxanthinstereoisomers in thermally processed vegetables one literary composition, the document is published in Food Chemistry 92 (2005) 753-763.
3. the analysis of zeaxanthin steric configuration
The present invention adopts magnetic nuclear resonance method that the steric configuration of zeaxanthin in the product is analyzed, specific analytical method is with reference to Application of HPLC coupled with DAD, method in APcI-MS and NMR to theanalysis of lutein and zeaxanthin stereoisomers in thermally processed vegetables one literary composition, the document is published in Food Chemistry 92 (2005) 753-763.
In addition, the marigold extractum commodity that following embodiment of the present invention adopted are available from middleization (Qingdao) Bioisystech Co., Ltd, and this product appearance is the dark-brown thick liquid.
Embodiment 1
2.0kg marigold extractum, 1.08kg sodium methylate, 2 gram acetate and 10 liters of methyl alcohol are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 96～102 ℃ of reactions stopped heating after 28 hours;
When temperature in the kettle drops to 45 ℃, filter; With methanol wash filter cake 1 time, wash filter cake again with water 3 times, add 2.4g antioxidant TBHQ, 75 ℃ of oven dry 8h, thick product 240g.After testing, zeaxanthin: xenthophylls (mol ratio)=88.10: 9.71 contains the quality percentage composition 65% of zeaxanthin.
Embodiment 2
1.5kg marigold extractum, 1.68kg potassium hydroxide, 4.5 gram sodium borohydrides and 10.5 liters of Virahols are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～3MPa, 116～122 ℃ of reactions stopped heating after 19 hours;
When temperature in the kettle drops to 80 ℃, filter; With washed with isopropyl alcohol filter cake 1 time, use the washing with alcohol filter cake again 3 times, add 1.8g antioxidant TBHQ, 40 ℃ of oven dry 10h, thick product 180g.After testing, zeaxanthin: xenthophylls (mol ratio)=88.21: 9.68 contains the quality percentage composition 62% of zeaxanthin.
Embodiment 3
1.8kg marigold extractum, 1.75kg sodium ethylate, 0.18 gram oxalic acid and 9 liters of methyl alcohol are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 102～108 ℃ of reactions stopped heating after 18 hours;
When temperature in the kettle drops to 40 ℃, filter; With washed with methanol filter cake 3 times, wash filter cake again with water 1 time, add 2.11g antioxidant TBHQ, 70 ℃ of oven dry 10h, thick product 211g.After testing, zeaxanthin: xenthophylls (mol ratio)=84.51: 12.96 contains the quality percentage composition 61% of zeaxanthin.
Embodiment 4
1.5kg marigold extractum, 2.88kg sodium ethylate, 15 gram oxalic acid and 18 liters of sherwood oils are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.2MPa～4MPa, 107～113 ℃ of reactions stopped heating after 18 hours;
When temperature in the kettle drops to 60 ℃, filter; Clean filter cake 2 times with sherwood oil, wash filter cake again with water 2 times, add 1.65g antioxidant vitamin C, 65 ℃ of oven dry 12h get thick product 165g.After testing, zeaxanthin: xenthophylls (mol ratio)=88.32: 9.71 contains the quality percentage composition 63% of zeaxanthin.
Embodiment 5
1.5kg marigold extractum, 2.8kg potassium methylate, 3 gram propionic acid and 7.5 liters of propyl carbinols are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～1.5MPa, 102～108 ℃ of reactions stopped heating after 20 hours;
When temperature in the kettle drops to 55 ℃, filter; Clean filter cake 1 time with propyl carbinol, with water washing filter cake 3 times, add 1.5g antioxidant TBHQ again, 60 ℃ of oven dry 16h, thick product 150g.After testing, zeaxanthin: xenthophylls (mol ratio)=88.15: 9.72 contains the quality percentage composition 61% of zeaxanthin.
Embodiment 6
1.8kg marigold extractum, 4.0kg potassium ethylate, 18 gram acetate and 12.6 liters of heptane are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 108～114 ℃ of reactions stopped heating after 18 hours;
When temperature in the kettle drops to 45 ℃, filter; With washed with heptane filter cake 2 times, wash filter cake again with water 2 times, add 1.98g antioxidant vitamin E, 70 ℃ of oven dry 10h, thick product 198g.After testing, zeaxanthin: xenthophylls (mol ratio)=88.35: 9.69 contains the quality percentage composition 63.2% of zeaxanthin.
Embodiment 7
1.0kg marigold extractum, 1.26kg sodium hydroxide, 50 gram acetate and 9 liters of toluene are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 104～110 ℃ of reactions stopped heating after 36 hours;
When temperature in the kettle drops to 45 ℃, filter; Clean filter cake 1 time with toluene, washing with alcohol filter cake 2 times washes filter cake with water 1 time again, adds 1.14g antioxidant TBHQ, and 65 ℃ of oven dry 14h get thick product 114g.After testing, zeaxanthin: xenthophylls (mol ratio)=87.26: 10.01 contains the quality percentage composition 60% of zeaxanthin.
Embodiment 8
2.0kg marigold extractum, 5.0kg saleratus, 6 gram propionic acid and 24 liters of hexanes are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 102～108 ℃ of reactions stopped heating after 30 hours;
When temperature in the kettle drops to 55 ℃, filter; Clean filter cake 1 time with hexane, use the washing with alcohol filter cake again 3 times, add 2.18g antioxidant TBHQ, 50 ℃ of oven dry 8h get thick product 218g.After testing, zeaxanthin: xenthophylls (mol ratio)=88.10: 9.81 contains the quality percentage composition 66% of zeaxanthin.
Embodiment 9
1.0kg marigold extractum, 1.12kg potassium hydroxide, 50 gram acetate and 5 liters of ethanol are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 104～110 ℃ of reactions stopped heating after 30 hours;
When temperature in the kettle drops to 60 ℃, filter; Clean filter cake 3 times with ethanol, wash filter cake again with water 1 time, add antioxidant: 0.5gTBHQ and 0.55g vitamins C, 65 ℃ of oven dry 12h get thick product 105g.After testing, zeaxanthin: xenthophylls (mol ratio)=87.01: 11.21 contains the quality percentage composition 57% of zeaxanthin.
Embodiment 10
1.5kg marigold extractum, 7.5kg yellow soda ash, 1.5 gram oxalic acid and 13.5 liters of Virahols are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 102～108 ℃ of reactions stopped heating after 24 hours;
When temperature in the kettle drops to 70 ℃, filter; Clean filter cake 3 times with Virahol, wash filter cake again with water 1 time, add 1.59g antioxidant TBHQ, 75 ℃ of oven dry 8h get thick product 159g.After testing, zeaxanthin: xenthophylls (mol ratio)=85.23: 11.01 contains the quality percentage composition 60% of zeaxanthin.
Embodiment 11
2.0kg marigold extractum, 4.5kg sodium bicarbonate, 3 gram formic acid and 14 liters of propyl carbinols are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 106～112 ℃ of reactions stopped heating after 31 hours;
When temperature in the kettle drops to 70 ℃, filter; Clean filter cake 3 times with propyl carbinol, with washing with alcohol filter cake 1 time, add 2.2g antioxidant vitamin E again, 50 ℃ of oven dry 10h, thick product 220g.After testing, zeaxanthin: xenthophylls (mol ratio)=84.23: 13.40 contains the quality percentage composition 60% of zeaxanthin.
Embodiment 12
2.0kg marigold extractum, 5kg salt of wormwood, 0.2 gram formic acid and 18 liters of methyl alcohol-propyl carbinols (volume 1: 1) mixing solutions are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～1MPa, 104～110 ℃ of reactions stopped heating after 22 hours;
When temperature in the kettle drops to 45 ℃, filter; With washed with methanol filter cake 3 times, wash filter cake again with water 1 time, add 2.01g antioxidant TBHQ, 65 ℃ of oven dry 15h, thick product 201g.After testing, zeaxanthin: xenthophylls (mol ratio)=85.21: 12.54 contains the quality percentage composition 65.8% of zeaxanthin.
Embodiment 13
1.0kg marigold extractum, 0.56kg sodium hydroxide, 30 gram acetate and 7.0 liters of methyl alcohol are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 106～114 ℃ of reactions stopped heating after 33 hours;
When temperature in the kettle drops to 55 ℃, filter; With washed with methanol filter cake 3 times, wash filter cake again with water 1 time, add 1.04g antioxidant TBHQ, 70 ℃ of oven dry 10h, thick product 104g.After testing, zeaxanthin: xenthophylls (mol ratio)=86.52: 10.98 contains the quality percentage composition 56% of zeaxanthin.
Embodiment 14
1.0kg marigold extractum, 2.88kg sodium hydroxide, 2 gram sodium borohydrides and 12 liters of benzene are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 100～106 ℃ of reactions stopped heating after 24 hours;
When temperature in the kettle drops to 50 ℃, filter; Clean filter cake 2 times with Virahol, use the washing with alcohol filter cake again 2 times, add 1.08g antioxidant TBHQ, 60 ℃ of oven dry 8h get thick product 108g.After testing, zeaxanthin: xenthophylls (mol ratio)=87.21: 10.58 contains the quality percentage composition 62% of zeaxanthin.
Embodiment 15
1.8kg marigold extractum, 1.82kg sodium hydroxide, 3.6 gram formic acid and 16.0 liters of methyl alcohol are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 106～112 ℃ of reactions stopped heating after 20 hours;
When temperature in the kettle drops to 55 ℃, filter; With methanol wash filter cake 1 time, use the methanol wash filter cake again 3 times, add 2.3g combination antioxidant (vitamin-E+Ascorbyl Palmitate=3: 2, mass ratio), 40 ℃ of oven dry 16h, thick product 230g.
The thick product of gained is dissolved in chloroform, and fully stirring and dissolving is filtered; Concentrate chloroform, 4 degree are recrystallization down.
Obtain product 180g, after testing, zeaxanthin: xenthophylls (mol ratio)=88.42: 9.67 contains the quality percentage composition 83.11% of zeaxanthin.
Embodiment 16
1.8kg marigold extractum, 9kg sodium methylate, 54 gram formic acid and 21.6 liters of toluene are added to reactor, fully stir; Closed reactor, nitrogen replacement; 0.1MPa～2MPa, 106～112 ℃ of reactions stopped heating after 22 hours;
When temperature in the kettle drops to 55 ℃, filter; With washed with methanol filter cake 3 times, use the washing with alcohol filter cake again 1 time, add 2.02g antioxidant TBHQ, 40 ℃ of oven dry 14h, thick product 202g.
The thick product of gained is dissolved in chloroform, and fully stirring and dissolving is filtered; Concentrate chloroform, 4 degree are recrystallization down.
Obtain product 162g, after testing, zeaxanthin: xenthophylls (mol ratio)=86.52: 11.25 contains the quality percentage composition 77.87% of zeaxanthin.
Claims (9)
1. the preparation of compositions method that contains zeaxanthin, it is characterized in that this method is included in the closed reactor, will through or be dissolved in organic solvent through pretreated natural product or the xenthophylls that contains xenthophylls, and add the alkaline catalysts of 2～20M and the auxiliary agent of raw materials quality 0.01～5%, under 90～130 ℃ of conditions of temperature, react 12～36h;
Auxiliary agent wherein is selected from formic acid, acetate, oxalic acid, propionic acid or sodium borohydride.
2. the preparation of compositions method that contains zeaxanthin according to claim 1 is characterized in that described auxiliary agent is formic acid or sodium borohydride.
3. the preparation of compositions method that contains zeaxanthin according to claim 1 is characterized in that described alkaline catalysts is selected from sodium hydroxide, calcium hydroxide, potassium hydroxide, sodium methylate, sodium ethylate, yellow soda ash, salt of wormwood, sodium bicarbonate, saleratus, potassium methylate or potassium ethylate.
4. according to claim 1, the 2 or 3 described preparation of compositions methods that contain zeaxanthin, it is characterized in that described organic solvent is selected from the mixed solvent that two or more solvent is formed with arbitrary proportion in hexane, heptane, sherwood oil, methyl alcohol, ethanol, Virahol, propyl carbinol, benzene, toluene or the above-mentioned solvent.
5. the preparation of compositions method that contains zeaxanthin according to claim 4 is characterized in that this method comprises the steps:
1. in reactor, add reaction raw materials, organic solvent, isomerization reaction alkaline catalysts and auxiliary agent, wherein, the consumption of organic solvent is 5～12 times of (volumes: quality) of reaction raw materials; Base catalyst concentration is 2～10M; Described auxiliary agent is formic acid or sodium borohydride, and its addition is 0.1～3% of a raw materials quality;
2. in the closed reactor, nitrogen replacement at pressure 0MPa～4MPa, reacts 12～36h under 90～130 ℃ of conditions of temperature;
3. behind the stopped reaction, be cooled to 40～80 ℃, filter;
4. the gained filter cake is washed 3～8 times with cleaning solvent, described cleaning solvent is selected from water, methyl alcohol, ethanol, Virahol, normal hexane, sherwood oil, acetone, and each time washing can be chosen different cleaning solvents;
5. washed after-filtration, added antioxidant, 30～80 ℃ of oven dry 2～24h.
6. the preparation of compositions method that contains zeaxanthin according to claim 5 is characterized in that described step cleaning solvent 4. is selected from water, methyl alcohol, ethanol or sherwood oil.
7. the preparation of compositions method that contains zeaxanthin according to claim 5 is characterized in that antioxidant during described step 5. is selected from TBHQ, vitamin-E, vitamins C, sodium ascorbate, dimension C cetylate, BHT or above-mentioned two or more antioxidant mixes the mixture of forming with arbitrary proportion.
8. according to claim 5, the 6 or 7 described preparation of compositions methods that contain zeaxanthin, it is characterized in that 5. described step has before added the purification step of recrystallization, carry out recrystallization after the employing extraction solvent extracts fully; Wherein, extraction solvent is selected from chloroform, tetrahydrofuran (THF), ethyl acetate, acetone or methylene dichloride; Recrystallization solvent is selected from chloroform, tetrahydrofuran (THF), ethyl acetate, acetone, methylene dichloride, or mixed solvent that mix to form with arbitrary proportion of two or more solvent wherein.
9. the preparation of compositions method that contains zeaxanthin according to claim 8 is characterized in that recrystallization temperature is lower than 6 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101589121A CN101182302B (en) | 2007-12-14 | 2007-12-14 | Method for preparing compositions containing zeaxanthin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101589121A CN101182302B (en) | 2007-12-14 | 2007-12-14 | Method for preparing compositions containing zeaxanthin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101182302A CN101182302A (en) | 2008-05-21 |
| CN101182302B true CN101182302B (en) | 2010-08-18 |
Family
ID=39447742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007101589121A Active CN101182302B (en) | 2007-12-14 | 2007-12-14 | Method for preparing compositions containing zeaxanthin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101182302B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014008851A1 (en) | 2012-07-12 | 2014-01-16 | 浙江医药股份有限公司新昌制药厂 | Method for preparing high level of zeaxanthin |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101781240B (en) * | 2010-01-07 | 2014-06-04 | 浙江医药股份有限公司新昌制药厂 | Method for preparing xanthin crystals with high zeaxanthin content by using vegetable oil resin as raw materials |
| CN105085351A (en) * | 2015-09-22 | 2015-11-25 | 哈尔滨宝德生物技术股份有限公司 | Technology for converting lutein into zeaxanthin |
| CN106977439B (en) * | 2017-03-23 | 2018-10-02 | 广州智特奇生物科技股份有限公司 | A kind of isomerization method of lutein |
| CN114957072A (en) * | 2021-02-25 | 2022-08-30 | 内蒙古昶辉生物科技股份有限公司 | Method for preparing zeaxanthin and zeaxanthin pellet from marigold ointment |
-
2007
- 2007-12-14 CN CN2007101589121A patent/CN101182302B/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014008851A1 (en) | 2012-07-12 | 2014-01-16 | 浙江医药股份有限公司新昌制药厂 | Method for preparing high level of zeaxanthin |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101182302A (en) | 2008-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101182302B (en) | Method for preparing compositions containing zeaxanthin | |
| Bortolini et al. | Metal catalysis in oxidation by peroxides. 27. Anionic molybdenum-picolinate N-oxido-peroxo complex: an effective oxidant of primary and secondary alcohols in nonpolar solvents | |
| Kim et al. | Hg2+-selective fluoroionophoric behavior of pyrene appended diazatetrathia-crown ether | |
| Shiga et al. | Azo-crown ethers. The dyes with azo group directly involved in the crown ether skeleton | |
| CN101909729A (en) | Ozonolysis Reaction in Liquid CO2 and CO2 Expansion Solvent | |
| Lu et al. | A new method for ellagic acid production from pomegranate husk | |
| CN101274915B (en) | Method for synthesizing isoxazole | |
| CN110452147B (en) | Preparation method of beta-carotene | |
| CN101941958B (en) | Method for preparing 5-hydroxymethyl furfural and 2,5-furandimethanol simultaneously | |
| CN102659717A (en) | Synthetic method of 2-methyl-1-(4'-methylthiophenyl)-2-morpholinyl-1-acetone | |
| CN108947758A (en) | A method of catalysis dibenzofurans open loop prepares biphenyl | |
| CN102746203B (en) | Preparation method of high-content zeaxanthin | |
| CN104530019A (en) | Method for synthesizing VE nicotinate | |
| Pratt et al. | Identification of rutin and isoquercitrin in cottonseed | |
| CN105777679B (en) | A kind of benzodihydropyran ring derivatives and preparation method thereof | |
| CN105399653A (en) | Industrialization method for preparing zeaxanthine from marigold oil resin in one step | |
| Ogata et al. | Kinetics of the reaction of p-benzoquinone with sodium thiosulfate | |
| CN118255828A (en) | Synthesis method of tetraene acetate | |
| CN102816142A (en) | Synthesis method for pentadecanoicacid | |
| CN203178186U (en) | Real-time esterification and carbonylation reaction on-line analysis system for ethylene glycol production industry through synthesis gas | |
| CN102260231A (en) | Preparation method of ascorbyl palmitate | |
| CN102816153A (en) | Method for synthesizing vitamin E (VE) nicotinate | |
| Howard et al. | Fungal metabolites. Part III. Isolation of secalonic acids from Phoma terrestris | |
| Krauss et al. | Molecular signal transduction by conformational transmission | |
| CN110256323B (en) | A method for synthesizing indole from coal-based ethylene glycol and aniline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: 116600 Dalian medical science and Technology Development Zone, Liaoning 49, Dalian Patentee after: Dalian promise biological Limited by Share Ltd Address before: 116600 Dalian economic and Technological Development Zone, Liaoning Province, No. seven northeast street, No. 18 Patentee before: Dalian Innobioactives Co., Ltd. |